Patent GB-1397622-A (GB)
Title: Cysteine salts
IPC: C07D307/38
Filed: 1972-10-27
Abstract: 1397622 Compositions comprising cysteine salts L'OREAL 27 Oct 1972 [28 Oct 1971] 49700/72 Addition to 1223961 Heading A5B [Also in Division C2] A composition suitable for application to at least one of the hair, scalp and skin comprises, with a suitable vehicle, as active ingredient at least one salt of the formula: in which: n is 2 or 3; R 3  is selected from either: definition (a): (i) a linear or branched alkyl radical with up to 18 carbon atoms, an alkenyl radical with 3 to 18 carbon atoms, an alkyl radical with 2 to 4 carbon atoms substituted by one or two hydroxyl radicals or a -C(C 6 H 5 ) 3  radical, (ii) a -(CH 2 ) m -CH (OR) 2  radical in which R represents an alkyl radical with 1 to 4 carbon atoms and m is 1 or 2, (iii) a radical of the formula -(CH 2 ) p -R 5  in which either R 5  represents a 2-thienyl radical and p=1 or R 5  represents -C 6 H 5 , a 2-pyridyl radical or a 2-pyridyl-N-oxide radical and p=0, 1 or 2, or (iv) a radical of the formula: or a radical of the formula: in which q is 0 or 1 and A, represents hydrogen or a radical A', which is a nicotinyl radical, a radical of the formula -COR 7  or -SO 2 R' 7  in which R 7  represents hydrogen, an alkyl radical with 1 to 18 carbon atoms, an alkenyl radical with 2 to 18 carbon atoms, a -CF 3  radical, a radical of the formula: in which r is 0 or 1 and R 8  represents hydrogen, an alkyl radical with 1 to 4 carbon atoms, an alkoxy radical with 1 to 4 carbon atoms, halogen or an acetamido radical, and R' 7  represents an alkyl radical with 1 to 4 carbon atoms or a radical of the formula: R 8  being as defined above; or definition (b): (v) a radical of the formula: in which s is 1 or 2 and B is (vi) a radical of the formula -(CH 2 ) t - NHCONH 2  in which t is 2 or 3, (vii) a radical of the formula -(CH 2 ) u -R 11  in which R 11  either represents 1-naphthyl or 2-naphthyl, in which case u is 0 or 1, or 2-tetrahydrofuryl or 2-furyl in which case u=1, or a 2-pyridyl radical substituted by halogen or an alkyl radical with 1 to 4 carbon atoms in which case u is 0, 1 or 2, (viii) a radical of the farmula: in which v is 0, 1 or 2 and w is 1, 2 or 3, R 12  is halogen, an alkoxy radical with 1 to 5 carbon atoms or a branched or unbranched alkyl radical with up to 4 carbon atoms such that if w is 1, R 12  can: additionally be an alkylsulphonyl, dialkylamino, alkylthio or alkylsulphinyl radical, the alkyl groups of which contain 1 to 4 carbon atoms, or a phenoxy, cyclohexyl, methylenedioxy, nitro or trifluoromethyl radical, (ix) a -CH(C 6 H 5 ) 2 , -CH (C 6 H 4 -p-OCH 3 ) 2  or -C(CH 3 ) 2  (C 6 H 4 -p- OCH 3 ) radical, or (x) a -R 13 -S-(CH 2 ) n -NH 2  radical in which n is as defined above and R 13  is an alkylene radical with 2 to 4 carbon atoms, optionally substituted by 1 or 2 hydroxyl radicals, a butenylene radical or a radical of the formula: -(CH 2 ) 2 -SO 2 -(CH 2 ) 2 -; A represents either: (i) hydrogen in which case R 4  represents a -(CH 2 ) z -COOH radical, z being 1 to 5, and in this case R 3  is as defined in definition (b), or (ii) -CONH 2 , or (iii) a radical as defined under A' 1 , or (iv) a -CO-CH 2 -CH 2 -COOH radical, such that when A is as defined under (ii), (iii) or (iv), R 4  is selected from either: definition (a): a -C(C 6 H 5 ) 3 , -CH(C 6 H 5 ) 2 , -CH 2 -C 6 H 5 , or -(CH 2 ) z -COOH radical in which z is 1 to 5, or definition (b): (i) a linear or branched alkyl radical with up to 18 carbon atoms, an alkenyl radical with 3 to 18 carbon atoms or an alkyl radical with 2 to 4 carbon atoms substituted by 1 or 2 hydroxyl radicals, (ii) a radical of the formula -CH 2 (CH 2 )- q -CH 2 - NHA 2 , in which q is 0 or 1 and A 2  represents a -CONH 2  or -CO-CH 2 -CH 2 -COOH radical or a radical as defined under A' 1 , (iii) a radical of the formula -(CH 2 ) m -CH(OR) 2  or of the formula IV above in which m, R, B and s are as defined above, (iv) a radical of the formula -(CH 2 ) 1 -R 14  in which R 14  represents: either a 1-naphthyl or 2-naphthyl radical, in which case 1 is 0 or 1, or a 2- thienyl, 2-furyl or 2-tetrahydrofuryl radical, in which case 1 is 1, or a 2-pyridyl-N-oxide, or 2-pyridyl radical, optionally substituted by halogen or an alkyl radical with 1 to 4 carbon atoms, in which case 1 is 0, 1 or 2, (v) a radical of the formula V above in which v, w and R 12  are as defined above, (vi) a -C 6 H 5 , -(CH 2 ) 2 -C 6 H 5 , -CH(C 6 H 4 -p-OCH 3 ) 4  or -C(CH 3 ) 2 -(C 6 H 4 -p-OCH 3 ) radical with (vii) or a -R 13 -S-CH 2 -CH-COOH radical in NHA 2  which R 13  and A 2  are as defined above, x and y being 1 or 2 such that the number of free amino groups in the compound is the same as the number of free carboxylic acid groups, with the proviso that at least one of R 3  and R 4  represents a radical of a definition (b). The compositions may be used topically or orally and may be, for example, in the form of a permanent waving composition, shampoo, cream, milk, gel, dermatological block, aerosol foam, aqueous or aqueous alcoholic lotions, flavoured drinks and tablets.